Substituted aryl onium materials
View Patent ↗Acid generators comprising a carbocyclic or heteroaromatic group substituted with at least one diester moiety are provided. These acid generators are particularly useful as a photoresist composition component.
1. A photoresist composition that comprises an acid generator that comprises a structure of Formula (I):a
wherein Z is a counter anion;
X is sulfur or iodine;
R 0 is hydrogen or a non-hydrogen substituent;
R′ and R″ are the same or different non-hydrogen substituents and optionally may form a ring, provided that if X is iodine, one of R′ and R″ is absent;
W is —C(═O)O(CX′X″)nC(═O)O—, wherein n is a positive integer and each X′ and X″ is independently a hydrogen or non-hydrogen substituent;
A is an optionally substituted carbocyclic aryl or optionally substituted heteroaromatic group;
Q is optionally substituted alkylene, optionally substituted alkenylene, or optionally substituted alkynylene; and
E and E′ are each independently hydrogen or a non-hydrogen substituent, with at least one of E and E′ being a non-hydrogen substituent.
2. The photoresist composition of claim 1 wherein Z 31 is selected from the group consisting of carboxylate, sulfamate, or non-fluorinated sulfonate.
3. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 2 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.
4. The photoresist composition of claim 1 wherein Z 31 contains a polymerizable moiety.
5. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 4 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.
6. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 1 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.
7. A photoresist composition that comprises an acid generator comprising a structure of Formula (II):
wherein Z is a counter anion;
R is —(CX′X″)nC(═O)OR, wherein n is a positive integer, each X′ and X″ is independently a hydrogen or non-hydrogen substituent, and R′ is a non-hydrogen substituent;
each T, each T′ and each T″ are the same or different non-hydrogen substituent, wherein either of T and T″ or T and T′ are capable of joining to form a ring;
n, n′ and n″ are each independently 0, 1, 2, 3 or 4;
J represents a chemical bond, or a group capable of covalently linking B and C;
Q is a C 1 -C 8 saturated or unsaturated alkylene group;
E and E′ are each independently hydrogen or a non-hydrogen substituent, with at least one of E and E′ being a non-hydrogen substituent; and
A, B, and C are each the same or different optionally substituted carbocyclic aryl or heteroaromatic groups.
8. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 7 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.
9. The photoresist composition of claim 7 wherein J represents a chemical bond.
10. The photoresist composition of claim 7 wherein J represents a group capable of covalently linking B and C.
11. The photoresist composition of claim 10 wherein J is optionally substituted alkylene group C═O, O, SO, SO 2 , NH, or NR where R is a non-hydrogen substituent.
12. The photoresist composition of claim 10 wherein J is an ether, ester, amide, carbonate, sulfortate, sulforte, or sulfonamide.
13. The photoresist composition of claim 7 wherein Z 31 is selected from the group consisting of carboxylate, sulfamate, or non-fluorinated sulfonate.
14. The photoresist composition of claim 7 wherein Z 31 contains a polymerizable moiety.
15. A photoresist composition that comprises an acid generator comprising a structure of Formula (IIa):
wherein Z is a counter anion;
R is —(CX′X″)nC(═O)OR, wherein n is a positive integer, each X′ and X″ is independently a hydrogen or non-hydrogen substituent, and R′ is a non-hydrogen substituent;
each T, each T′ and each T″ are the same or different non-hydrogen substituent, wherein either of T and T″ or T and T′ are capable of joining to form a ring;
n, n′ and n″ are 0, 1, 2, 3 or 4;
R a and R b are each H, or R a and R b taken together represent a chemical bond or a group capable of covalently linking B and C;
Q is a C 1 -8 saturated or unsaturated alkylene group;
E and E′ are each independently hydrogen or a non-hydrogen substituent, with at least one of E and E′ being a non-hydrogen substituent; and
A, B, and C are each the same or different optionally substituted carbocyclic aryl or heteroaromatic groups.
16. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 15 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.
17. The photoresist composition of claim 15 wherein R a and R b are each H.
18. The photoresist composition of claim 15 wherein R a and R b taken together represent a chemical bond or a group capable of covalently linking B and C.
19. The photoresist composition of claim 15 wherein Z 31 is selected from the group consisting of carboxylate, sulfamate, or non-fluorinated sulfonate.
20. The photoresist composition of claim 15 wherein Z 31 contains a polymerizable moiety.
21. An acid generator that comprises a structure of Formula (VII):
wherein
Z is a counter anion;
R is hydrogen or a non-hydrogen substituent;
each T, each T′ and each T″ are the same or different non-hydrogen substituent, wherein either of T and T″ or T and T′ are capable of joining to form a ring;
n is 0, 1, 2, 3 or 4;
n′ and n″ are each independently 0, 1, 2, 3, 4 or 5;
E is hydrogen or a non-hydrogen substituent;
A′, B′, C′ are each independently a C 6 -C 36 aromatic, C 5 -C 36 polyaromatic, or C 5 -C 36 conjugated aromatic group;
J′ represents no bond, a single chemical bond, or a group capable of covalently linking B′ and C′;
R 5 is hydrogen or a non-hydrogen substituent; and
Q′ 3 is a C 1-8 alkylene group.
22. A photoresist composition that comprises an acid generator of claim 21 .
23. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 22 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.
24. An acid generator that comprises a structure selected from the group consisting of:
25. A photoresist composition that comprises an acid generator of claim 24 .
26. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 25 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.